Among the items to be sold at the auction in Beverly Hills on 30 November are:

:: Hefner’s personal set of bound volumes of Playboy magazine which is expected to go for between $20,000 and $40,000 (£15,000-30,000).

Image:A book about Hefner’s sex life is included in the sale Pic: Julien’s Auctions

:: A vintage 1946 coin-operated Wurlitzer jukebox programmed by Hefner from his game house containing 24 original 78 rpm record albums by artists such as Artie Shaw, Frank Sinatra, Harry James, Johnny Mercer, Lena Horne and others. It is expected to fetch between $10,000 and $20,000 (£7,500-£15,500)

Image:Various trinkets and two ashtrays carved into a nude woman are among the collection Pic: Julien’s Auctions

:: A custom 1974 Monopoly board game that includes a pipe smoking Hefner and a Playboy Bunny, among other Mansion regulars, custom Hefner Monopoly money, houses, hotels, cards and more in a custom wooden box marked ‘Monopoly Parts for HMH’ valued at $6,000-$8,000 (£4,000-6,000)

:: Hefner’s personal copy of the first issue of Playboy magazine in 1953 featuring Marilyn Monroe on the cover. It is said to be worth between $3,000-$5,000 (£2,300-£3,890)

Image:His sailor hat is up for grabs. Pic: Julien’s Auctions

:: A range of furniture includes a carved oak chair valued at $400 to $600 (£313-£469) and a tiger print sofa, valued at $1,500 to $2,000 (£1,174-£1,565).

The tycoon’s boudoir in the Playboy Mansion has been revealed ahead of the auction and shows a wall covered in photos of him and various women.

Martin Nolan, director of Julien’s Auctions which is organising the sale, said: “Julien’s Auctions is honoured to present this extraordinary auction event that celebrates pop culture icon Hugh Hefner, whose life and legacy truly embodied the American dream.”

Image:The Playboy boss’s vast wardrobe. Pic: Julien’s Auctions

Money raised from the auction will go to the Hugh M Hefner Foundation which was established in 1964 to support civil rights and civil liberties, with special emphasis on First Amendment rights and “rational” sex and drug policies.

Christie Hefner, president of the HMH Foundation, said: “Whether it was building his company into one of the most recognisable global brands in history or standing up for social, sexual and civil rights causes, my father lived an extraordinary life as a publishing, social and cultural pioneer and left a legacy that his foundation will perpetuate.

Image:Items from the tycoon’s games room are up for sale. Pic: Julien’s Auctions

“We are very proud to announce that 100% of the auction proceeds will benefit the foundation that works to advance his life’s commitment to individual rights in a free society.”